The Derby Turnpike Company was formed in 1798 with capital of about $7500 and 10 stockholders. Joseph Wheeler and others petitioned the General Assembly for a charter stating that “the road now leading from Derby landing to the New Haven Court House is extremely bad, hilly, crooked and rough so as to be almost impassible for teams and carriages; that a new road or highway might be laid out from said landing to said Court House which would shorten the distance two miles and be laid over good level and feasible land.” The road was about 8 miles in length and 18 feet wide but it was made known that where there were rocks or other obstructions making the 18 feet impossible, the road was to be made as wide as possible.
The limits of the road were from the house of Eneas Monson on York Street in New Haven to the house of Joseph Wheeler at Derby Landing. Derby was a prosperous village at the time and the import trade was booming as ships came up the Housatonic River from foreign ports, especially from the West Indies. Trade with that part of the world had been lucrative when Milford Colony’s very own, Alexander and Richard Bryan built ships in 1645 that sailed there and to Boston Harbor giving the colony a stature only known in Boston at that time. A tollgate was built near the Maltby Lakes on the turnpike and the house, although altered somewhat, can still be seen just before the large billboards on the right.
A picture of the tollhouse with its signage can be seen at the Academy and due to an error in judgment by the lawyer who tended to the sale of the tollhouse in the 1920s, the sign was given to the New Haven Historical Society where it hangs today. A replica of the sign can be seen at the Academy. Certain exemptions were allowed such as persons traveling to and from public worship, funerals, society or town meetings, military travel and farmers going to and from gristmills. I should think that a commercial venture would be charged as a profit was being made in the grinding. Farmers tending to their farming duties were not liable for the toll. By 1887 a resolution was passed to “hire” the New Haven and Derby Turnpike for the free use of the inhabitants of Orange not to exceed $240 each year. By 1897, the toll road was discontinued. Having acquired the road, Orange voted to appropriate $3000 to make improvements.
Now, to the house on the falls on the Wepawaug River, you see with the road being upgraded, it made sense to the Alling family to build a suitable tavern for weary travelers as they made their way up the turnpike. Built with two enormous chimneys, one of which had a large smoker box built into it, the prospect of many guests was obvious, allowing for eight fireplaces to serve the public. Well, the public was not served as noted in Mary Woodruff’s “History of Orange” because the traders went past the Alling Tavern into New Haven. The house is two stories high built on what was called a rubble foundation. Once having clapboards, the house maintained its 18th century “look”, an inviting structure at the time. The windows on the ends were typical of the Greek Revival style and the porch sported the identification of Italianate. Changes that occurred over the years:
The floor joists showed sections of bark, as they were hand hewn with wide floorboards throughout. A massive stairway, curved as it ascended to the 2nd floor making a grand entrance upon opening the front door with its decorative carved glass panels. The four fireplaces on each floor were each treated differently as the years passed but the brick chimney, once the strength of the home began to show wear. The 2nd floor was almost identical to the first with rooms on either side of the massive staircase.
A number of the elements in the Alling Tavern suggest a late 18th century or early 19th century construction for the main portion of the house. The structure in the attic and cellar exhibit the hand-hewn beams that are pegged, and beautiful, wide floorboards in the attic were fit for any room on the first and 2nd floors keeping with the tradition of using good wood throughout. The two massive chimneys and stature of the home give rise to a wealthy owner and we know that the Allings were successful with various mills up and down the Wepawaug River just south of the house, ultimately moving into Derby. There was a sawmill, just west of the river owned by Garret DeWitt as far back as 1776, a convenient source for the large, expansive tavern.
The stained, split shingles that have been so apparent, covered at least two layers of clapboards and asphalt shingles replaced the original wooden ones on the roof. With additions to the back of the house, a fireplace was added in the cellar. All of the history, changes and ownership of the house has been its worst enemy as can be seen today, a skeleton of its former glory. Purchased from the Regional Water Authority, its new owner, a restoration contractor, had great plans of restoring the house as his family home. Beginning with the removal of the shingles which were damaged with age, the clapboards were revealed only to be taken off as well being damaged beyond saving.
What could not be seen from the outside nor from the inside plaster walls was the insidious workings of insects and dampness, both entities rotting the structure from within. Upon inspection by the Regional Water Authority, the Connecticut Preservation Trust and myself, it is apparent, more than apparent, that the house must be demolished. The upside is that all portions of the structure that are salvageable will be incorporated into a new house, with the identical footprint, inside and out, a testimony to its former life. All elements such as fireplace surrounds, flooring, roof joists and staircases will be returned and the Alling Tavern will once again stand on the edge of the dam at the Wepawaug River. Although the chimneys were badly cracked, the old bricks can be used to rebuild the fireplaces. The house was architecturally significant in its time being an example of late 18th century, with its decorative changes, the Greek Revival staircase, the Italianate and Aesthetic mantels, Italianate porch and door.
A good example of the adaptation of an older house to fit new uses and will once again be visible on the dam at the Wepawaug River.